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Direct and Regioselective Di‐α‐fucosylation on the Secondary Rim of β‐Cyclodextrin
Author(s) -
Verkhnyatskaya Stella A.,
de Vries Alex H.,
Doumade Vries Elmatine,
Sneep Renze J. L.,
Walvoort Marthe T. C.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201806090
Subject(s) - fucosylation , cyclodextrin , regioselectivity , glycosylation , chemistry , fucose , molecular dynamics , fragmentation (computing) , combinatorial chemistry , chromatography , organic chemistry , computational chemistry , glycoprotein , computer science , biochemistry , catalysis , operating system
A straightforward glycosylation method is described to regio‐ and stereoselectively introduce two α‐ l ‐fucose moieties directly to the secondary rim of β‐cyclodextrin. Using NMR and MS fragmentation studies, the nonasaccharide structure was determined, which was also visualized using molecular dynamics simulations. The reported glycosylation method proved to be robust on gram‐scale, and may be generally applied to directly glycosylate β‐cyclodextrins to make well‐defined multivalent glycoclusters.